


First Dates Before Breakfast

by Houkangishi



Category: Supernatural
Genre: Anal Sex, BDSM, Blow Jobs, Bottom!Cas, Light Bondage, M/M, Spanking, Sub!Sam, Threesome, Threesome - M/M/M, Top!Sam, Wincestiel - Freeform, dom!Dean, sub!cas, top!dean
Language: English
Status: Completed
Published: 2015-07-21
Updated: 2015-07-21
Packaged: 2018-04-10 12:49:10
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,367
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4392506
Author URL: https://archiveofourown.org/users/Houkangishi/pseuds/Houkangishi
Summary: <blockquote class="userstuff">
              <p>Castiel never expected his first night at Dean's to lead to a morning like this.</p>
            </blockquote>





	First Dates Before Breakfast

**Author's Note:**

> I've never written smut before. I decided to go big for my first attempt to try to make subsequent attempts easier.
> 
> The one thing I wasn't sure how to tag is the fact that Cas agrees to a scene in the moment. It's not really dub-con, but it's not really the greatest practice to be in the habit of. . . 
> 
> As with most fanfiction, this portrayal of BDSM is for fun, and not entirely accurate, nor is everything done in the safest way.

Castiel was an early riser. He had never needed much sleep and often found himself watching the sunrise from his apartment balcony with a cup of tea. This morning instead of his stunning view of the city, he was watching the light creep over a privacy fence and into a small well-tended garden off of an aged back deck. He grimaced as he took a sip of coffee. This was one of the reasons why he generally didn't stay over after dates. It seemed like no one ever had good tea or raw honey.  But, his date with Dean had gone really well. So well that when the man had told him to stay, he hadn't wanted to leave. 

When he had taken his father's '66 mustang in to be restored, he had been shocked to hit it off so spectacularly with the young mechanic. He discovered Dean had inherited the shop from his surrogate father and built a solid reputation for being the best restoration shop within 300 miles. They started out chatting when Castiel called to check on the car, and then Dean had told him he was buying him dinner. That first date they had both felt each other out and danced around the elephant in the room. Finally, over dessert Dean said, "I only consider sex great if my partner feels it for a week." with a wink.  Castiel had nearly come in his pants.

It took three more dates, a few phone calls, and countless text messages before he had finally ended up on his knees for Dean the night before. They had hashed out hard lines, traded test result, and spent time getting to know one another outside the bedroom before jumping into a physical relationship.

He was startled out of his quiet reminiscing about the previous evening by a slamming cabinet and a low groan. "Out of mini wheat's again!"

Castiel turned around, surprised to find that it wasn’t Dean who had joined him in the kitchen, but a tall man with floppy hair and gangly limbs. He was dressed in low slung flannel pajama pants and was now fiddling with the Keurig. He was gorgeous, if still a little younger (though not much honestly) than Castiel normally went for. All tan skin and the tight muscles that the end of adolescence afforded.

 Castiel shifted around nervously, all too aware of the fact that he was wearing only a stolen pair of sweat pants himself, and that his back certainly had a few welts. Dean hadn't mentioned a roommate, but it made sense that the young mechanic wouldn't live alone in a house of this size. The man continued to fix his coffee, oblivious it seemed to not being alone in the room. Castiel cleared his throat. "Good morning." He greeted, his voice still gravelly from sleep.

"Oh you're up." The other man said with no real surprise in his voice. He finally turned to face Castiel. "Dean's friends usually sneak out after he's left for work. He should be up any time now." He stepped forward and held out a hand. "I'm Sam by the way. Dean's brother." Castiel shook his hand.

"Castiel," he replied.

"Oh I know." Sam grinned, leaning back against the counter behind him. "Dean hasn't been able to shut up about you for weeks. All he's been able to talk about is how he wants to bend you over Baby's hood." Sam looked him up and down, making Castiel all too aware of his underdressed state and various bite marks, before quirking one eyebrow and smirking. "I can see why." He picked up his mug of coffee and gently blew away some of the steam, maintaining a heated stare with Castiel.

Castiel blushed and mumbled a thank you, slightly disconcerted by his date's brother and his open ogling. He was just about to make his excuses back to the bedroom when Dean shuffled into the kitchen in a well-worn pair of boxer briefs. Castiel took a moment to appreciate the view Dean's underdressed form offered.

"Morning Sammy," Dean mumbled, stealing the coffee cup out of his brother's hands in exchange for a quick kiss that was relatively chaste, but still left Castiel dumbfounded. "Morning Cas." He shuffled over and gave Castiel a slightly longer, though equally lazy, kiss. He hopped up on the kitchen counter and took a swig of his coffee, immediately brightening. "So what were you two talking about?"

Castiel took another sip of his coffee and nearly spit it right back out when Sam answered, "About how much I agree with your assessment that Cas here was made for taking a cock."

Dean frowned thoughtfully, the silence stretching out for a long minute. "You weren't thinking of playing with my toy without me, were you Sammy?" His voice was low and dangerous as he set down his mug, sending a shiver through Castiel.

Sam suddenly looked a little bashful, squirming under Dean's focus and mumbling out "No Dean." While still confused by the brothers' behavior, Cas was glad he wasn't the only one feeling the effects of that voice.

"Come here Cas." Cas jumped in surprise at being addressed before cautiously making his way over to Dean. Dean plucked the coffee out of his hand and set it down next the other mug. Dean pulled him in close and kissed him possessively, one hand in his hair, holding him in place. Just when Cas had almost forgotten about their audience, Dean pulled back and spoke lowly directly into his ear. "I want to watch him fuck you." Cas shivered. "I want to tell him how to take you apart and put you back together. I want to watch you come on his cock and then feel how open you are when he's done." Dean paused, giving him a chance to take in his words. "I know we haven't talked about this. I didn't plan for this to happen this way. Do you want to stop and talk about this, or let it play out?" Cas moved to glance over at Sam and Dean grabbed his chin, keeping his Cas's gaze fixed on him. "Eyes on me Angel. If you want to keep playing, it's still my rules."

Cas tried to calm himself down enough to think it through, but Dean's words kept bouncing around in his head. He was harder than he had ever been, including the night before when Dean had kept him from coming for hours. They were brothers. It should seem wrong what he was saying, but somehow it just made it hotter. The thought that these two so casually shared kinks and lovers, to the point that the wrongness didn't even seem to faze them anymore.

Cas swallowed, his decision made by the persistent image of these two striking men sharing him. He nodded once "I need to hear you say it Angel." Dean purred.

"Yes Dean." Cas pulled back to look the taller man in the eyes. "I think I would enjoy that Sir."

Dean's eyes took on a dangerous gleam, and he grinned a little madly. "First rule of this game. Keep your eyes on me. Now, Come with me." He hopped down off the counter, forcing Cas to take a step back and grabbed his hand, pulling Cas along behind him and out of the kitchen. "Playroom Sammy. Now." Dean called back over his shoulder, voice carrying the assured authority of someone who was used to being obeyed. Cas didn't turn to look, but could hear Sam padding along behind them.

When Dean pulled him past his bedroom door, Cas was a little confused. They had scened in Dean's room the night before, and so when the other man had mentioned the playroom, Cas had naturally assumed that's where they were headed. When they entered the room at the end of the hall that Cas had assumed during his brief trip to the bathroom was a guestroom, Cas could see why Dean had forgone using it their first night together.

The wall to the left of the door was a large closet. The sliding doors were open on one side and Cas could see over Dean's shoulder a whole array of equipment. Dildos, rope, butt plugs, floggers, paddles, spreader bars, and gags were all within site. It was neatly organized and almost looked unused for how pristine everything appeared to be. The back wall had a large mirror with a simple twin bed set horizontally in front of it, a set of shackles on each of the four corners and room to move between the mirror and the mattress. Next to that was a spanking bench and further down the wall was an honest to goodness saint Andrews cross. Cas didn't think anyone actually had one of those and eyed it warily. On the third wall was a door that looked like it led to an en-suite bathroom and an overstuffed leather chair. Finally, in the last corner was what looked like a nest of cushions. The rest of the room was empty with plenty of floor space. As Cas stepped into the room, he could feel that the carpet was soft and thick with plenty of padding underneath. He felt a tap on the side of his face.

"Eyes on me Angel." Dean said, snapping Cas's gaze back to him. "If I catch them wandering again I am going to blindfold you."

"Yes sir." Cas said, eyes now fixed on Dean though he could feel Sam's presence behind him.

Dean walked further into the room and took a seat in the overstuffed chair. He beckoned the two other men closer until they were side by side about 4 feet from him. "Sammy, go get Cas a cushion. Angel." Dean paused and grinned again. "Strip."

The command was simple and expected but Cas could still feel himself blushing. His hands fumbled at the tie of his borrowed sweatpants and as soon as the knot came undone they pooled at his feet. Dean raised an eyebrow at his lack of underwear and rubbed a palm over the obvious erection tenting his boxer briefs. "I think I could get used to you wearing my clothes commando." Cas' blush deepened and he fought the urge to look at his feet.

Out of the corner of his eye, Cas watched Sam come back over and place a large oval cushion at his feet.

Dean motioned to the cushion "I want you kneel there Angel, hands behind your back until I'm ready for you," he turned his gaze to Sam. "I have to deal with Sammy's punishment first." Dean crooked his finger and Sam stepped forward. Faster, and with more dexterity than Cas would have expected, Dean had reached up and grabbed Sammy by the back of the neck, pulling the younger man across his lap with what sounded like a low growl.

Cas shakily lowered himself to his knees, arms already locked behind his back to keep from touching himself without permission. The show of strength from Dean had left him practically leaking onto the floor.

Dean manhandled Sammy into the position he wanted him, the taller man not struggling, but not helping. When he was finally settled with his hands wrapped around Dean's ankles and weight resting on the older man's thighs, Dean leaned down close. He wrapped a fist in Sam's hair and used it to pull his head up so he could see Dean's face, back arched at an uncomfortable angle, and spoke in a low hushed voice Cas could barely hear. "This is what happens when you think about touching my toys without permission Sammy. One of these days you will learn to ask." He released Sam's hair and straightened up, now speaking in a normal tone. "Let's start with twenty and see how you feel hm?" Dean pulled Sam's pajama pants and underwear down to just below his ass. "Cas will count for us." Dean grinned at Cas. "Won't you Angel."

Cas nodded, slack jaw before remembering himself and clearing his throat. "Yes Sir."

Dean's grin didn't fade as he rubbed a hand over Sam's ass and squeezing a handful before pulling back and bringing his hand down with a resounding 'SMACK'

"One." Cas' voice was horse and strained with arousal as a bright red hand print bloomed in Dean's wake. Dean's hand fell again. 'SMACK' "Two." And again 'SMACK' "Three" Cas' voice cracked. He could see Sam squirming in the bottom of his vision. He continued to count as Dean methodically turned his brother's ass a bright red. He couldn't help but wonder if Sam was hard, or if the friction of Sam rocking under his blows was driving Dean as mad with lust as he felt. Even though he couldn't see it, Cas could just imagine the blissed out look on Sam's tear streaked face as he let out the most beautiful sobbed out moans with every strike of Dean's palm.

When "Twenty!" fell urgently from Cas' lips, he wanted nothing more than to crawl forward and beg Dean to let him take Sam's place, but wasn’t sure he would even finish getting into position without coming. He took deep breaths, eyes fixed on Dean's chin to calm his wildly beating heart.

Dean was smoothing his hand along Sam's nicely reddened ass and smirking at Cas' obvious distress. "I think Sammy here has had enough. Don't you?" Dean didn't give Cas a chance to answer. "On your feet Angel. I want you to go and kneel on the bed, facing the mirror, pretty ass in the air. You can use the mirror to keep your eyes on me. Do you understand?"

"Yes sir." Cas answered.

He stood as gracefully as he could and backed up until he could see the mirror and Bed from the corner of his eye. He quickly and carefully turned his head until his eyes meant Dean's in the mirror. "Good boy." He barely heard Dean murmur.

Cas climbed onto the bed, noting the softness of the plain chocolate sheets. He kept his eyes fixed on Dean's as he wrapped his fingers into the sheet at the edge of the bed and lowered his chest to rest between them. His knees were drawn up under him and his feet dangled just off the edge, leaving him exposed and vulnerable.

He watched as Dean helped Sam straighten up and then step out of his pajama pants. He stepped up to his brother and whispered something Cas couldn't hear. Sam was trembling, face and cock flushed as he nodded. Cas's eyes widened. He had thought Dean was large, and he was certainly slightly thicker, but held nothing on his taller sibling in the length department.

The two brothers walked over to the bed together slowly. Dean settled himself at the head of the bed, perpendicular to Cas' own body and where Cas could easily see him in the mirror. He was still wearing his underwear, but the front was straining and wet with arousal. Sam came to stand behind Cas. He started to reach out, but one look at Dean had the taller man drawing his hand back. "Kneel down Sammy." Dean's voice was still steady and hypnotic. Cas couldn't see Sam's actions, but the young man must have obeyed his brother because Dean's face broke into a satisfied grin. "You both look beautiful like this. Flushed with arousal, on your knees, cocks hard and leaking." He paused as if considering something. "I wonder how long I could leave you like this? My very own living art." He reached his hand into his boxer briefs and pulled his cock out, stroking it lazily. Both Sam and Cas groaned with longing, causing Dean to just lean back and stroke himself in earnest. "I could just get myself off, leave you two here covered in my drying come."

Cas moaned loudly and tried to push his hips down, but couldn’t get the friction he needed at this angle. Dean slowed his hand after another moment and collected some pre-come on his fingers. He shifted on the bed and used his other hand to grasp Cas by the hair and turn his face toward him. He reached forward and painted his wet fingers over Cas' lips. "So good for me," he said softly before leaning forward and kissing Cas fiercely. Dean rested his forehead against Cas'.

A moment later he pulled away and kneeled next to him. Cas could only see his back in the mirror and was surprised when he felt what had to be Dean's hands pull his ass cheeks apart. "Get him nice and wet Sammy. No hands yet."

Cas felt Sam's long hair brush over his ass first and then there was a warm tongue dragging over his hole. He let out a long groan, fighting the urge to bury his head into the mattress. When Sam started tentatively working his tongue inside of Cas, it was Dean who let out a guttural sound of his own. "Does he taste good Sammy?" Dean dropped his voice a little. "Does he taste like me?" Cas could feel Sam's own pleasured sound vibrating through him. "Does that turn you on? Knowing you're eating out the ass I came in just a few hours ago? He's probably still a little open and sloppy and here you are gobbling it up. Are you that hungry for your big brother come. Should we make Cas wait and watch you suck me down instead?" Cas couldn't help but press his ass back against Sam at the image that brought to mind. Dean threw a wicked grin at Cas in the mirror. "You like that idea too Angel? Should we tie you up and see if you can get off just from watching my brother swallow my cock?"

Cas panted out a desperate "Yes sir."

Dean chuckled and reached one hand forward to ruffle Cas' hair, making both Sam and Cas whimper at the reduced access Sam had. "Maybe next time Angel." He smacked Cas' ass once. "This time is all about making sure you and Sammy here get to know one each other properly." Dean reached down and wrapped his hand in Sam's long hair, using it to pull his face away from Cas ass. He reached behind him and pulled out the lube. Cas heard the cap click open and watched as Dean tipped the bottle. He felt the cool substance pour over and into his hole and shivered at the sensation. After Dean had poured out enough that the lube was running down Cas' balls, he motioned for Sammy to hold out his hand and poured some more into his palm. "He's tight Sammy, so take your time and get him nice and open."

Sam didn't waste any time, immediately inserting two fingers into Cas and starting to scissor gently. Dean smirked again and stepped around to stand in front of Cas.

Dean gripped Cas' hair in his hand and pulled his head back so the shorter man was looking up at him. Cas met his eyes and followed the tug until his face was more level with Dean's crotch. Dean used his free hand to get his cock out. He ran the head lightly over Cas' lips. "Lick." The order was short but Cas followed it with enthusiasm, using whatever range of motion Dean would give him to trail his tongue over Dean's length. "Stop watching me Sammy and get back to work."

Cas hadn't noticed the fingers inside him had stopped, but he did notice the pleasant stretch as a third one slipped in. He pressed his lips against the head of Dean's cock in a near reverent kiss. "Good boys." Dean murmured, taking a moment to just enjoy watching the two other men.

Dean ran his hand down Cas' cheek, an almost soft look in his eyes. "Open up for us." He murmured. Cas opened his mouth and Dean pushed in. The three of them stayed like that for a few minutes, Dean thrusting into his mouth shallowly while Sam worked him open, carefully avoiding his prostate.

"How's he doing Sammy?" Dean finally asked his brother.

"I think he's ready." Sam's voice was strangled and eager, his fingers relentless.

Dean pulled out of Cas' mouth and dropped a quick kiss to his forehead before walking over to the closet. He rummaged around for a minute before coming back towards the bed with a set of leather padded cuffs and a foil packet. "Stand up Sammy, hands behind your back." The taller man did as he was instructed, pulling his fingers out of Cas' ass gingerly.

Cas could see Dean standing behind Sam in the mirror. He could here the buckles on the cuffs as Dean fit them around Sam's wrists. When they were in place Dean reached around and slid a condom over Sam's cock. "I'm going to let Cas here do all the work for you Sammy. " Dean said, urging the other man forward. "Raise that ass a little higher Angel." Cas did as instructed. He could feel the blunt latex covered head of Sam's cock against his hole. "You ready?" Dean met his eyes in the mirror.

"Yes sir." Cas answered breathlessly and he started pushing back. Dean held the base of Sam's cock in one hand and Placed the other on Sam's lower back, helping him sink into the smaller man's heat.

Cas was shaking as Sam bottomed put in him. Dean traced a finger around his stretched out hole, making him want move. "Beautiful." He heard the other man whisper. Dean allowed him a moments pause. "Now fuck yourself on him."

It was an awkward position, but Cas managed to get a good rhythm going, Sam brushing against his prostate. He wasn't sure at what point it happened but his eyes locked with Dean's in the mirror and he found himself chanting "please please please," breathlessly.

Cas felt like he was going to explode. "Look at him Sammy. He's about to come just from fucking himself on your dick." Dean ran a hand down Cas' back. "Such a good little slut for us." Dean cracked a hand against Cas ass again, causing the other two men to gasp and groan. "Come for us Angel."

It only took a few more thrusts and Cas felt the tension in his body crest as he came untouched all over the sheets below him.

Dean came around the bed a little more hurried than he had planned, sinking to his knees in front of Cas and taking his face in his hands even as Sam whimpered behind them. "So beautiful for us Angel." Dean wiped away tears Cas had barely even felt. "Are okay to keep going or do you want to watch Sammy and I?"

"I'm good." Cas' voice was scratchy. He pushed himself forward to kiss Dean.

Dean grinned and stood back up.

"Sammy," Dean put his hands on his brother's hips. "On your back on the bed, facing me."

Cas felt Sam pull out and scooted over to let the larger man lie down. He felt Dean's hands on his hips pulling him backwards. "Stand up and turn to face me." Cas did as he was told.  Dean maneuvered him over. "I want you to face me while sitting on his dick. You can look away only as much as you need to to safely get into position."

Cas swung a leg over Sam's lap and grabbed the other man's cock, guiding it back into him. When he was fully seated he looked up at Dean, fighting the urge to squirm. "Now lean forward and suck my cock. Sammy, you can fuck him now."

Cas leaned forward and took as much of Dean's cock into his mouth as he could while Sam thruster into him. It was awkward at first as Sam struggled to find a rhythm with his arms trapped under him.

The pace was brutal. Cas let Sam's frantic thrusts push him further onto Dean's cock while Dean pushed forward into his mouth. All Cas could do was hold onto Dean's hips and suck in breaths whenever the other man pulled out far enough.

"You close Sammy?" Dean asked, voice strained as he watched the two other men.

"Yes." Sam hissed, the s long and drawn out.

"Come on then Sammy. I'm almost there and if I come on his face before you're done, you can finish by yourself  later." Sammy made a desperate whine in the back of his throat and his hips picked up a frantic, desperate pace.

It was only a few more moments before Cas felt Sam's hips drive up one last time and still as the taller man let out a wordless shout. Dean groaned above him and pulled out of Cas' mouth. He wrapped his hand tightly around his cock and with a few quick tugs was coming over Cas' face. "Beautiful." Dean murmured between pants. Once he caught his breath he carefully helped Cas off of Sam and laid him out next to his brother.

Cas felt boneless as he watched Dean remove Sam's cuffs and rub feeling back into his arms. Once Sam was comfortable Dean went about cleaning them all off, smiling goofily to himself every time he met either Cas or Sam's eyes.

Finally he collapsed down between them and kissed them both on the forehead. The bed was too small for three grown men, but they were okay with the tangled limbs and awkward angles for the moment.

"Are you both okay?" Dean asked quietly.

Cas grinned. "I think it's safe to say that was a satisfactory first date for Sam and I."

Dean raised an eyebrow. "You want to do this again?"

Cas cocked his head to the side. "I do believe that is what first implies Dean. Sam?"

For the first time since the scene started Cas looked Sam in the eye. Sam chuckled "Hell yeah."

Dean grinned and pulled both men tighter to his chest. He grimaced after a moment. "I think we are gonna need a bigger bed in here."


End file.
